There are a number of good harnesses. First, what to avoid. Steer clear of cheap harnesses - they will not hold the dildo securely enough, they tend to be uncomfortable to wear and ultimately aren't worth the money.

The "two-strap" style of harness has much better stability than the single strap style that runs between butt cheeks (and gets in the way if you want any action with your lady parts). As with all toys, I say buy once and buy quality. Sure, you can get an inexpensive beginner's kit that will give you an idea of what pegging is like, but most couples go straight from the kit to something more comfortable and better made pretty quickly, so why waste your money? If you have serious doubts either of you will like pegging, buy a quality dildo, experiment with it handheld and with the DIY harness first, and if you both enjoy it, save your money to buy a quality harness to go with it.

Harnesses made from leather are strong, luxurious, comfortable and yummy, in that way that only soft, supple leather can be. Leather is a porous material and for the purists in hygiene, is not meant to be shared because it is not sterilizable. Make sure you have a set of O-rings to fit a variety of size toys. Ruby's favorite leather harnesses? Aslan Leather. Two favorite styles? Jaguar and the Minx. The Minx is especially good for lovely large bodies, especially with large upper thighs. The corset back adds extra stability for BBWs and the leg straps comfortably allow for all that loveliness.

Fabric harnesses are quite comfortable and washable. Ease of care makes the fabric harnesses a choice for many. Once done with play you simply throw it in a lingerie bag and then into the washer. Make sure the measurements of the harness will accommodate the wearer. I have the Spareparts Joque. I have to say this harness wins the comfort and easy care awards. Plus it can be used for both flare-based dildos as well as doubles. Here's my review of the Joque.

Other things to consider when selecting a harness...How high or low does the harness sit and will that give her the pressure in the place she wants? Or will it press uncomfortably on the pubic bone? Some harnesses have special pockets for a bullet vibe. Some women love them. Some women don't like the hard bullet between their clitoral area and the base of the toy. Would she enjoy vibration against her clit? There are indeed toys that can provide that. I know it sounds silly but some women don't want to think about having an orgasm while pegging in the beginning, they just want to learn how to fuck someone first and add the quest for orgasm later. Also, if you anticipate using a double, be sure that the harness you choose is compatible with a double, some aren't.

Ahhhh...so many dildos, so little time. First let's talk materials. Silicone is the very best material for it's ability to be sterilized, and durability - two very important factors. Educate yourself about safe, quality toys. Don't get toxic, poor quality dildos - no matter how cheap! You cannot sterilize them and they will expose your body to bad chemicals. My favorite silicone dildos are Fuze or Tantus.

Make sure your dildo will fit snugly in the ring of the harness. If you have a harness that allows you to change the O-ring, you might need different O-rings to fit different toys. And don't let your eyes be bigger than your ass and buy something too big! That happens more often than you might think. Also, don't let your apprehension prevent you from selecting anything larger than your finger - you might as well just use your finger. Practice moderation - 1.25" diameter and 5.5 - 6 " in length works for most beginners. Size and shape can be very individual. Some men love ridges...some don't. Some men say it's the girth that gets them off, others say it's the length and position of the dildo.

Dual density dildos have a softer outer layer for comfort and a more rigid inner core for functionality. They are made for comfort, but also to mimic the feel of a real cock. Please be aware that most of the dildos of this type are sub-standard materials, which can harbor bacteria. Dual density dildos made from 100% silicone do indeed exist! My favorite dual density (softer outside and rigid inside) dildos are the Real Nude line.

A word about double-ended dildos like the Tango, Share and the Feeldoe. Most couples find that these cannot be used without a harness, no matter how sexy that may be to envision. More about that here. I would like to emphasize that they are on the advanced end of pegging toys for the majority of people. Some couples love them, but almost all women need a harness to hold them in. The difficulties arise from a) vaginal muscles being no match against the anal sphincter so they are difficult for most women to even keep in, b) the insertion point is the only point of balance as opposed to a nice snug two strap harness which will let you push up, down and sideways and c) imagine dealing with all that when you are just learning how to fuck for the first time! Not recommended for beginners, especially for women who are even a little reluctant about pegging - you don't want the additional complicating factor to put her off pegging forever.

Keep in mind that no one lube works for everyone, because people have allergies to all kinds of things. Having said that, my holy grail of pegging lubes is Sliquid Silk, which is a hybrid silicone/water-based lube. It is definitely compatible with good quality silicone toys, so don't worry about that. And don't get the organic kind! it contains Aloe Vera in it, which dries up the lube while pegging = not good. Sliquid is an amazing company that makes a variety of excellent quality lubes.

Coconut oil is also a pretty good lube for pegging if you run out of lube!

5) What's the best position?

Depends on what you want to achieve...

Missionary rates high for intimacy (face to face), high for prostate stimulation and high for access to his cock. Depending on how a man's testicles hang, he may need to hold them up while you thrust...or end up with sore balls the next day. She can hold his legs up, he can hold his legs up, she can put his legs over her shoulders or you can use a sex-sling to do the work for you. Missionary is not the easiest position for beginners.

Doggy Style (the man on all fours and the woman behind) rates high for the woman's visuals, high for ass access (for spanking) and medium for cock access (reach around).

Side Saddle is where the man lays on his side with his top leg bent and pulled up towards his chest. She straddles his bottom leg with her knees. Eye contact and cock accessibility are both pretty good. This is an excellent position for women who are shorter from knee to hip. His knee pulled up allows for easier penetration and the side laying allows for relaxation as well. Here's a visual for you!

Cowboy rates high for comfort for the woman, lack of pegging skills by the woman (he's doing the riding) high for prostate stimulation (he rides it how it feels best) and high for cock access.

Reverse Cowboy (the man faces her feet) rates high for ass access (spanking), high for the woman's visuals and high for prostate stimulation (he rides it how it feels best).

The Chairman rates high for intimacy (face to face), high for woman's comfort and high for prostate stimulation (he rides it how it feels best).

Bulldog (Advanced): The man on his hands and knees and the woman above and behind him with her legs on the outside of his. Here is the visual (with genders reversed). Rates very high for prostate stimulation and high for both ass access and visuals. The woman needs to have very strong thigh muscles. (I didn't know this was the name of the position but knew about the website of animated sexual positions and was fairly sure I could find an example with the genders reversed - voilà !)

With all these positions...there are so many variables. Let me give you just one example from my personal experience. My legs are quite long (36" inseam). The distance from my hip to my knee is longer than most people I know. That meant with Doggy Style I had to spread my legs very wide to be at the right height for his ass...so wide it was not as comfortable as it could have been. Pillows can be used to adjust heights sometimes, or if you want the best - get a Liberator sex cushion to play with.

6) It feels awkward...what are we doing wrong?

Nothing. It will feel awkward at first. Women were not born with cocks and it takes a while to get the hang of strapping one on. They also are not used to being the ones running the fuck. Men are normally not used to receiving and being vulnerable. Getting comfortable with something new just takes time. Keep your sense of humor, lower your expectations and have fun! Keep practicing.

7) Can she orgasm while pegging?

Absolutely. Not all women can orgasm while pegging their man, but many can, and there are different ways to reach that goal. One is to have a bullet vibe in the base of the dildo (in which case you need to make sure that the harness you use is open in the back so the base sits against her lady bits). One way is to buy a harness with a pocket on the back of it specifically made for a bullet vibe. One way is to have a double ended dildo that is stimulating her at the same time she is fucking him. There are some women who can orgasm simply from pressing against the harness while they are fucking their man. (Go back to the harness discussion for specifics and links.)

8) Can he orgasm while pegging?

Oh HELL yes. Absolutely. Again...not all men can orgasm while being pegged, but some can. This is where it gets a little involved, though. Some men have erections while they are being pegged. Some men don't. Some men have erections that come and go. Whether he is hard is not an indicator as to whether he is enjoying the pegging...it is just an individual thing...and nothing to worry about. So moving on to orgasms...a man can orgasm from combined cock stimulation and pegging, which men say is about 10 times as strong as an orgasm with just cock stimulation (and produces much more ejaculate). Some men can also orgasm just from pegging. A prostate orgasm for a man is very similar to a G-spot orgasm for a woman. And then there are men who can have multiple orgasms from prostate stimulation. So the answer to that is a big yes.

9) How can I try to minimize the mess?

Keeping it as clean as possible is a combination of diet, thorough showering, anal douching or enemas, and liberal use of towels because of the liberal use of lube. You will find more information about that in this article: "Keep it Clean, People". If you have never tried anal sex before, it is not normally as messy as you might imagine. Some people never douche or use enemas and don't have significant problems with messes.

Another thing you can do is to put down a Liberator Throe to protect to bed (or wherever you are pegging!) and contain the mess. The waterproof layer is perfect, and it's washer/dryer friendly, too.

10) How can I convince my woman to peg me?

The answer to that question is actually pretty involved. Read about it here.

11) How can I convince my man to let me peg him?

The answer to that question is pretty involved as well. You can tell him you found something that will give him an orgasm 10 times more powerful that anything he's ever experienced and produce a lot more come. That will do it for about 75% of sexually adventuresome men (okay, that's my own personal estimate with no studies to back the figures up, I admit). For the rest, or for the reluctant....read more here.

12) Why isn't he hard?

If he is not hard....don't freak out. There are a wide variety of penile responses to anal stimulation. While getting pegged some men will stay hard the entire time, some men's erections will come and go and some men's cocks will never get hard. Pay close attention here, though...his erection or lack thereof is not an accurate indicator of whether a man is enjoying the pegging. The best way to know whether your guy is having a pleasurable experience is to actually ask him. Good and open communication is essential during pegging, especially in the beginning. So keep asking if he likes what you are doing if you have any doubt. Some men have even reported that they do not like their cock stimulated during pegging because the sensations are different and it detracts from the prostate pleasure.

13) Why can't she fuck me like I fuck her?

Women...were not born with a cock. They need time to get used to it. So in the beginning it will seem awkward and hard to manage. From a man's perspective, it can be frustrating. The balance and natural roll of the hips takes time to perfect. The stamina takes time to build up. The muscles need time to develop. Which all means you just simply need to practice. Yay! It is likely your woman will appreciate you more once she dons a strap-on and fucks you - she will realize that the grace, strength, endurance and balance required to fuck is significant. You guys rock.

14) It just hurts - What are we doing wrong?

Pegging is not for every man. There are indeed some men who despite loving the idea of pegging, they do not feel any pleasure from their prostate or it's just painful and never gets any better. If you are following all the rules (go slow, use lots of lube, relax, bear down like you are trying to have a bowel movement, start small) then either he just isn't a man who enjoys pegging or there is a possibility he may have a medical condition (like hemorrhoids) that causes pain when his anus is penetrated. Best to check with a doctor if you have concerns in this area. Pain is an indicator - don't ignore it. Pegging done correctly should not be painful.

15) We can't find the prostate - Help!

Here is a map for you. Take a good look at it. The man should find a position that is comfortable for him. Face down with a couple of pillows under his hips is usually a good one. She sits on the bed behind him and uses her finger (gloved if preferred). If she has long fingernails fill the finger ends of a latex glove with cotton balls and then put on gloves before you begin. Anal exploration and long nails do not mix! You want to avoid tearing or scratching the rectal lining at all costs.

I like to use my middle finger, because it is the longest and the prostate can be difficult to reach sometimes. (I have met women who say their fingers are not long enough to reach their man's prostate and they have to use a toy.) Insert your finger about 2 inches and press downward toward his belly. Explore and get feedback about which spot feels the best. If he's turned on the prostate will be much easier to find. The more turned on he is, the more his prostate swells and can be located. When a man is about to come it's amazing how you can feel the prostate get bigger and harder and then release.

Like the G-spot, sometimes men have to sort of get used to feeling pleasure in that spot...it takes a while to wake it up. As long as it feels good, keep exploring and you'll find it eventually. Using your finger in the beginning is easier than using a toy. Once you know where the prostate is, positioning and angles of strap-ons and toys is easier to picture.

16) Where can I find a woman who will peg me?

Sorry guys, but there is no magic formula for finding a woman to peg you. In the end (pun intended) it's the same as looking for a woman to date. Read more about this here. If you have a partner and are trying to find a way to introduce her to the concept of pegging, I recorded a podcast exactly for that purpose. The best time for her to listen to it is after you have introduced the basic concept to her, because it addresses all her potential fears, concerns and misconceptions.Please be sure to listen to this podcast FIRST, because only you can decide if it is right for your partner. Podcast #112 - For the Ladies.

17) Where can I find a man to peg me?

The truth of the situation is that if you are a woman who loves pegging...you actually have your pick from a significantly large group of men who are looking for a woman just like you. You can explore FetLife(free) or OKCupid(free) or AdultFriendFinder($) and there will no doubt be groups of men bemoaning the fact that there are no women around to peg them. And I don't mean to sound negative about that. They are interested in pegging and sad/frustrated that there don't seem to be many women around who are into it. You will not have to look far.

In fact it may be more difficult to find a man who will approach you politely and respectfully when contacting you. There is something about the prospect of a woman with a strap-on that can turn reasonable men into crude dudes. The better ones will keep their enthusiasm in check and approach you with manners and style...as a person instead of a fetish delivery service.

18) Does the man have to be submissive?

Not at all. Many men do find that they feel somewhat submissive because the act of receiving pegging requires openness and vulnerability. But there is no rule that men must be submissive, nor is there any likelihood that a man will suddenly become effeminate just because he gets pegged.

19) Does the woman have to be dominant?

Not at all. Many women who are interested in pegging have dominant traits, but it is not necessary to be dominant. For a woman, pegging requires being the one to run the fuck, the active and giving role. This can be a new experience for her, but it does not mean she has to turn into a cold demanding bitch who wields absolute power over her guy link in porn (not that there's anything wrong with that, if that's your thing).

20) What if I don't want to reverse roles?

Then don't. Pegging can be a close, intimate and very sensual act between loving partners. There is really no need to look at it any way other than that. If you want to put your own particular kinky spin on it, then by all means go ahead, but that is entirely optional.

Now if there is something inherently mind-twisting about wearing a cock as a woman or getting penetrated as a man...well, that's just the mind fuck you are dealing with there. It can be a turn-on. But it can also freak you out a little. Take a deep breath and go with it.The rewards are extraordinary.

Always keep in communication with your partner. When trying something new sexually, it is good to have a debriefing after sex to talk about what you enjoyed, what worked, what felt weird...everything. Builds great sex partners and increases intimacy to do this...and not just with pegging!

21) Why do they call it "Pegging"?

Pegging is defined by Wikipedia as a sexual practice in which a woman penetrates a man’s anus with a strap-on dildo. The word “pegging” was popularized when it became the winning entry in a contest in Dan Savage’s Savage Love sex advice column, held after an observation was made that there was no common name for the act. the word can now be found in Wikipedia and the Urban Dictionary...and all over kinky websites!

22) What Questions have I missed?

Is there a pegging question you were looking for the answer to and you didn't find it here? Help me make this section more complete...go to the bottom of the page and click "Write Ruby" - send me your question!